Certificates and Encodings

At its core an X.509 certificate is a digital document that has been encoded and/or digitally signed according to RFC 5280.

In fact, the term X.509 certificate usually refers to the IETF’s PKIX Certificate and CRL Profile of the X.509 v3 certificate standard, as specified in RFC 5280, commonly referred to as PKIX for Public Key Infrastructure (X.509).

X509 File Extensions

The first thing we have to understand is what each type of file extension is. There is a lot of confusion about what DER, PEM, CRT, and CER are and many have incorrectly said that they are all interchangeable. While in certain cases some can be interchanged the best practice is to identify how your certificate is encoded and then label it correctly. Correctly labeled certificates will be much easier to manipulat

Encodings (also used as extensions)

.DER = The DER extension is used for binary DER encoded certificates. These files may also bear the CER or the CRT extension. Proper English usage would be “I have a DER encoded certificate” not “I have a DER certificate”.

.PEM = The PEM extension is used for different types of X.509v3 files which contain ASCII (Base64) armored data prefixed with a “—– BEGIN …” line.

Common Extensions

.CRT = The CRT extension is used for certificates. The certificates may be encoded as binary DER or as ASCII PEM. The CER and CRT extensions are nearly synonymous. Most common among *nix systems

CER = alternate form of .crt (Microsoft Convention) You can use MS to convert .crt to .cer (.both DER encoded .cer, or base64[PEM] encoded .cer) The .cer file extension is also recognized by IE as a command to run a MS cryptoAPI command (specifically rundll32.exe cryptext.dll,CryptExtOpenCER) which displays a dialogue for importing and/or viewing certificate contents.

.KEY = The KEY extension is used both for public and private PKCS#8 keys. The keys may be encoded as binary DER or as ASCII PEM.

The only time CRT and CER can safely be interchanged is when the encoding type can be identical. (ie PEM encoded CRT = PEM encoded CER)

Common OpenSSL Certificate Manipulations

There are four basic types of certificate manipulations. View, Transform, Combination , and Extraction

View

Even though PEM encoded certificates are ASCII they are not human readable. Here are some commands that will let you output the contents of a certificate in human readable form;

View PEM encoded certificate

Use the command that has the extension of your certificate replacing cert.xxx with the name of your certificate

Transform

Transforms can take one type of encoded certificate to another. (ie. PEM To DER conversion)

PEM to DER

openssl x509 -in cert.crt -outform der -out cert.der

DER to PEM

openssl x509 -in cert.crt -inform der -outform pem -out cert.pem

Combination

In some cases it is advantageous to combine multiple pieces of the X.509 infrastructure into a single file. One common example would be to combine both the private key and public key into the same certificate.

The easiest way to combine certs keys and chains is to convert each to a PEM encoded certificate then simple copy the contents of each file into a new file. This is suitable for combining files to use in applications like Apache.

Extraction

Some certs will come in a combined form. Where one file can contain any one of: Certificate, Private Key, Public Key, Signed Certificate, Certificate Authority (CA), and/or Authority Chain.

Openssl seems to be insisting on a non-empty pasrsowd at its prompt so its better todo it like this, specifing a null pasrsowd on the command line $ openssl pkcs12 -in certificate.p12 -out tempcrt.pem -passout pass:$ openssl x509 -in tempcrt.pem -noout -text -passin pass:$ rm tempcrt.pemThe -passin option also works on the initial command, its seen as insecure of course.

Approved: 11/13/2014

If you are planning on using a self sigend certificate, visit your server and export your certificate using Internet Explorer then email it to your iPhone (instructions can be found here)

Approved: 7/7/2014

Openssl seems to be insisting on a non-empty pasrowsd at its prompt so its better todo it like this, specifing a null pasrowsd on the command line $ openssl pkcs12 -in certificate.p12 -out tempcrt.pem -passout pass:$ openssl x509 -in tempcrt.pem -noout -text -passin pass:$ rm tempcrt.pemThe -passin option also works on the initial command, its seen as insecure of course.